


Hot, Sticky Sweet

by DRHPaints



Category: Conan O'Brien - Fandom, Conan O'Brien RPF, Late Night Host RPF, US Comedians RPF
Genre: 69 (Sex Position), Beard!Conan, Biting, Blow Jobs, Boss/Employee Relationship, Cunnilingus, Desk, Dom/sub Undertones, Explicit Language, Explicit Sexual Content, F/M, Face-Fucking, One Shot, Sir Kink, Smut, Spanking, Vaginal Fingering
Language: English
Status: Completed
Published: 2020-12-15
Updated: 2020-12-15
Packaged: 2021-03-10 23:20:07
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,453
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28095297
Author URL: https://archiveofourown.org/users/DRHPaints/pseuds/DRHPaints
Summary: After she gets worked up watching Conan do a desk washing promo for his new show on TBS, his producer Gwendolyn confesses her attraction and they go back to Conan's house for some fun.
Relationships: Conan O'Brien/Original Female Character(s)
Kudos: 6





	Hot, Sticky Sweet

**Author's Note:**

> If you haven't seen the video referenced in this fic, do yourself a favor. Pretty sure I'm responsible for half of those views, at least:  
> https://youtu.be/8evHC5LKKx0

There was no one else to blame. She knew that. Knew she condemned herself to this afternoon of torture. It wasn’t anyone else’s fault. She did it. Gwendolyn. She was the one. The one who, when Conan tapped a freckled finger to the corner of his thin lips during their meeting, looked around at those assembled and asked, “Hey, wouldn’t it be funny if…”

And Gwendolyn, emerald eyes a little too wide, head bobbing a tad too quickly, insistently responded, “Yeah. So so funny…”

So now here she stood, trapped under a pleasantly toasty Californian sunshine, breeze consoling her crimson waves as she examined the driveway set, condemned to stare at Conan’s tall, bearded frame alongside a desk, a bucket, and a hose.

“Alright.” Conan rubbed his large palms together, bouncing up and down on his toes. The man moved incessantly, Gwendolyn suspecting anxiety fueled that skinny physique. “Are we ready?”

With a nod the director, Stan, hovered over a boombox. “Yeah, I’ll hit play and you just do your thing.”

“Got it.” Ginger pompadour bopping, Conan clapped his hands and soon the sounds of Def Leppard’s  _ Pour Some Sugar On Me  _ flooded the air.

Without hesitation Conan bent down to the orange bucket from his considerable height, retrieving a yellow sponge. Turning back to camera, an impish heat behind those baby blue eyes sent a frustrated tingle between Gwendolyn’s thighs as Conan began wetting himself down. 

It was clear Conan thought himself silly. Clear many of those observing, the camera operator, Stan, Sona, believed the same. But Gwendolyn’s mouth filled with saliva and her knuckles grew white over her clipboard as Conan sank his pristine teeth into the sponge, blowing bubbles alluringly in her direction.

A cacophony of mock-porno music, irrepressible ‘boom-shaka-lacka’s,’ poured from his slivered lips as Conan tossed his long limbs around, gyrating like a maniac, Gwendolyn’s brain crafting increasingly wanton scenarios as she snapped her jaw shut, half a second short of drooling.

Plunging the sponge once again in the bucket, Conan slathered his gangly body over the desk, scrubbing seductively, pasty arms flexing.

_ Holy shit, why did I think I could handle this?  _ Gwendolyn bit her lip, breath shallow as Conan flipped over, buffing the desktop with his ass, face a commanding grimace before he hoisted himself up. Dancing on top of the desk, Gwendolyn felt as though she should’ve paid a cover charge to witness Conan’s captivating moves as his slender body twirled and he ripped a bite of sponge away with a snarl.

Of course he couldn’t resist drawing attention to his nonexistent ass, rubbing the sponge suggestively over himself, and despite being wound wire tight, Gwendolyn did laugh at that point before Conan hopped down.

Twisting on the water, Conan’s sky blue eyes teased as he brought his thin lips to the stream. Conan sprinkled over the soap addled desk for a moment before, Gwendolyn’s breath hitching, he turned the spray on himself.

Black t-shirt plastered to his lithe body, Conan ground himself up and down to the music, ginger hair slicking to his scalp. “Wait a second, I have an idea…” Conan leaned forward, wetting down his head before he dropped the hose. 

Whipping back his soaked tangerine tresses with an enticing air and swiping the moisture from his crystalline eyes, the flat out obscene expression decorating Conan’s chiseled features caused a violent pulse to echo through Gwendolyn’s pussy and she hoped no one heard her whisper, “ _ Oh fuck me _ …”

Conan retrieved the hose, shooting directly at their water-protected camera and for a second he tempted Gwendolyn to walk into the line of fire, get doused, perhaps have an excuse to change with him in the trailer afterward. And then maybe…

_ Okay, get it together… _ Gwendolyn chided herself as Conan wheeled out his orange chair. Sitting down and drawing up his freakishly long legs, Conan took hold of the edge of the desk, whipping himself around as the hose rained down above him, face a mask of jubilance before Stan mercifully yelled cut.

A soggy Conan squished his way toward them, droplets falling from his red beard as he perused the playback. “Okay,” Nodding, Gwendolyn tried not to gawk as Conan ran a hand over his sopping orange locks. “Good. I think we got it. Thanks, man.” Conan clapped Stan on the shoulder before glancing around with a chuckle. “Alright, anyone got a towel?”

“I’ll get it.” Gwendolyn piped up, returning to find Conan moseyed back near the desk as she handed him the terrycloth.

“Thanks Gwen.” Encasing his head in the towel, Conan emerged, sea blue eyes blinking, orange hair and beard mussed. “Mmm...that’s better.” Conan bunched up his slippery black shirt, squeezing a puddle out over the ground as he exposed his lightly muscled abs. “What?”

Gwendolyn didn’t realize she gawked, mouth dangling and emerald eyes saucers. “Oh, um…” Cheeks pinking, Gwendolyn shook herself back to reality, shoving away the persistent images of those big hands closing over her skin with a similar ferocity as they did the sodden fabric. “Nothing. Sorry.” 

Giving up, Conan peeled his shirt overhead, wringing out a stream and flapping it free. Once again Gwendolyn’s gaze wandered greedily over his narrow chest, the smattering of orange curlicues dabbling the pallid surface causing her to rest her weight forward on the balls of her feet. “Okay, what?” Conan chuckled, dipping down to meet her eye line with a broad grin.

Caught, Gwendolyn brought an ashamed hand to her brow. “Oh, um, sorry…” Gwendolyn stretched out her lower lip, turning away. “I didn’t mean to…it’s nothing…”

“No, what?” Drying off his midsection, Conan tilted his head curiously. “Don’t tell me I have a bat in the cave and you’re going to let me walk around all day looking like an idiot. Well…” Conan shrugged, smiling. “Like more of an idiot, I should say.”

Tittering apprehensively, Gwendolyn waved a dismissive hand. “No, um, it’s just…” Gwendolyn bit her inner cheek, unable to meet those piercing blue eyes. “You look...good.”

“Pfft.” Conan chuckled, glancing down at himself. “What?”

Clutching her clipboard to her chest, face a riotous red, Gwendolyn raised a timid shoulder. “Yeah, just...very...sexy…”

Hands going to his belly, Conan threw back his head and laughed, eyes scrunching. “You’re joking, right?” Conan narrowed his gaze suspiciously at her as he recovered.    
“I look like someone shaved Garfield from the neck down and threw him in the tub.”

Giggling, Gwendolyn shook her head, arms lowering. Gwendolyn found herself twisting on the spot, half a moment shy of twirling her hair and batting her eyelashes. “No, I...I mean it. You’re...hot. Sorry. I know…” Gwendolyn teetered her head, folding her lips under. “I know it’s unprofessional for me to say that.”

Mouth downturned in appraisal, Conan fell silent, continuing to remove the water from his shirt beneath his lengthy fingers. “So…” Studying the actions of his own hands, Conan nodded slowly. “Is it unprofessional if I say I don’t mind hearing that?”

Blue eyes locking into her own with mischievous intent, a smirk blossomed over Conan’s slender lips and goosebumps scattered across Gwendolyn’s skin. “I...I guess...maybe, but…” Swallowing, Gwendolyn grinned. “I’m glad to hear it.”

“Good.” Conan looped the towel over his neck, rocking back and forth on his heels for a moment as they quietly tiptoed toward one another along the tether of their gaze. “So…” Breaking away, Conan looked toward the street. “I have to change, but...after. You want to...get some dinner? Or something?”

Lungs hitching, Gwendolyn’s head bobbed without her instructing it to do so. “Yeah. Yeah, I’d like that.”

“Great.” Beaming, Conan’s fingers ghosted over her elbow and he walked backwards, reluctant to leave her face until the last possible second before he disappeared into the trailer. 

Gwendolyn hastily checked her reflection in the side mirror of Stan’s van, smoothing over her hair and jiggling herself into her bra before Conan stepped out, looking casually foxy in a dry pair of dark wash jeans and a Guinness t-shirt as he sauntered up.

“Hey.” Tipping his head down the street, Conan tucked his sizable hands in his pockets. “You ready?”

“Sure.” Gwendolyn followed Conan since she rode to the shooting location with the rest of the crew, delighted when he held the car door open for her with a smile.

“Alright, so…” Sticking the key in the ignition, Conan faced her, faint orange brow aloft. “What are you hungry for?”

Viridescent gaze starving and curvaceous lips parted, Gwendolyn’s murmur came out smoky and enticing. “Whatever you want...I’m...flexible…”

Fingers tightening on the wheel, Conan nodded carefully, cerulean eyes aflame with need. “Yeah, I...I could go for anything, I guess…”

“Yeah…” A beat of buzzing silence. A twitch of anxious fingers. Colliding with an urgency bordering on fury, tongues jammed into mouths and hands clawed at skin as Gwendolyn moaned with relief, threading into Conan’s damp orange locks as he practically hauled her into his lap.

“Fuck. Yes.” Gwendolyn managed to bite off the words before she tasted Conan’s slivered lips once more, his big hands grabbing her ass and dragging her near with a contented groan.

“Mmm...damn.” Leaving her mouth, Conan’s beard scratched as he kissed his way to Gwendolyn’s neck, agile fingers hugging her denim-clad thigh. “Not here…” Conan leaned back in the seat, taking a steadying breath as he met Gwendolyn’s gaze. “Do you want to come back to my place?”

“Hell yes.” Conan nodded and Gwendolyn sat back down, trembling hand doing up her seat belt as Conan pulled away. They made attempts at casual conversation, Conan trying to keep things light, to be his usual, funny self, but everything fell flat as the balloon of tension expanded, squishing them within the confines of the car, Gwendolyn exercising every modicum of restraint not to maul Conan as he drove.

Pulling into Conan’s garage was like standing before an oncoming tornado, sky green and earth shivering in anticipation as every hair on their bodies sizzled to attention. Conan purposefully didn’t look at Gwendolyn before he exited the car, knowing there was no way they’d make it into the house if he lost himself in those emerald eyes.

Opening her door, a freckled hand waited and Gwendolyn allowed Conan to lead her forward. “Come on…” Voice soft and head down, they meandered in slower than one might expect given the intensity of their attraction, but both Gwendolyn and Conan knew that once they crossed the threshold, once their feet strayed, the magnetism of their want would prove overwhelming, and these final dulcet moments allowed each of them a chance to compose themselves, to savor.

Shoes removed and door shut, Conan turned. “Gwen…” Blue eyes issuing an invitation her lips gratefully accepted, Conan molded around her, his tall body a reassuring canopy of lust. Fisting a hand in Gwendolyn’s auburn tresses, their tongues danced as Conan shuffled them backward to the couch.

Gwendolyn lifted Conan’s shirt overhead, admiring his body for the second time that day and moaning into his mouth as she finally got to flow her fingers over his wan speckled flesh. Knees bumping the couch, Gwendolyn broke from Conan to look over her shoulder, squealing delightedly when his wiry arms effortlessly scooped her up, draping her over the cushions.

Gwendolyn opened her legs as Conan settled atop her with a sensual roll of his long body, combing back her crimson hair as he scanned her face. “Damn Gwen, I’ve wanted you for so long. You know that?”

“Really?” Smiling, Gwendolyn polished Conan’s sharp cheek bone and he nodded. “Me too.” 

Conan rotated his hips, erection shockingly evident through their jeans as Gwendolyn rose to meet him and he swept in, mouth brushing over the sensitive skin below her ear. “Mmm...I’ve thought about doing so many things to you, Gwen…” Cupping her breast over the shirt, Gwendolyn’s nipples hardened almost painfully, the passage of fabric over taunting as she touched a kiss to Conan’s crisp jaw.

“Conan, I…” Struggling to formulate her thoughts as Conan’s body undulated above her, cock grinding hypnotically into the warmth between her thighs, Gwendolyn swallowed. “Me too. Fuck...Conan, just…” Gwendolyn arched her neck as Conan nipped at her ear, nails skipping over his freckled back. “Just fuck me.”

Leaning back, Conan’s ginger locks haloed his handsome face above her, though his thin lips sported a devilish grin. “Yeah?”

“Yes.” Gwendolyn nodded insistently, pelvis shamelessly continuing to rock against him despite Conan’s stilled body. “Do whatever you want. I just...take me. Now.”

“Mmm…” Conan bit his lip, leaning back to grab the hemline of her shirt and whip it free. Trickling a single finger down Gwendolyn’s abdomen, a tiny tremor crept into his reedy voice. “Whatever I want, huh?”

Bobbing her head, Gwendolyn slid her hand up Conan’s shapely thigh. “Yeah…”

In one lightning fast instant, Conan swatted her away, snatching Gwendolyn’s wrist and landing on top as he pinned her arm above her head. “Oh yeah, and what if…” Conan thrust his hips forward ruthlessly, cock bearing down and forcing the harsh denim against Gwendolyn’s sensitive clit in the most tantalizing of ways. “What if I want to boss you around a little? Huh?” Tearing down the front of her bra to free her ample breasts, Conan’s face smothered over them, beard itchy and lips supple as he sucked the pink nipples lasciviously. “You up for that, Gwen?”

Electrified by his ministrations, Gwendolyn’s free hand attempted to grope for Conan’s cock, but was heartily denied when he joined her wrists in one of his large palms overhead. “Yes.” Gwendolyn gasped, panties soaked as she rutted against him. “Yes,  _ fuck. Please!” _

“How about…” Ginger eyebrows wiggling, Conan took Gwendolyn’s chin with a half smile. “Please…’ _ sir’ _ ?”

“Oh, yes sir.” Adding a syrupy tone to her voice, Gwendolyn pouted bewitchingly. “Please. Fuck me, sir.”

Conan chuckled, popping open the button of her jeans. “Mmm...yeah. Gotta say…” Releasing her wrists long enough to rid Gwendolyn of her bottoms, Conan grinned. “I don’t hate that.”

Clasping her arms once more, Conan laid alongside her, his agile fingers petting the lips of her pussy as he drilled into Gwendolyn with an unrepentant cerulean stare. Gwendolyn’s lungs failed her, eyelids fluttering as Conan applied gentle pressure over her covered clit and he smiled. “Mmm...yeah. You like it when I play with this pretty pussy, don’t you?”

“Yeah…” Gwendolyn began, but when Conan’s hand stopped moving, she corrected herself. “Yes, sir.”

Deep chuckle rumbling up from his chest, Conan leaned in, his lips opening over her neck as his fingers parted her labia. Circling her clit with aching slowness, Conan’s voice descended into a well of erotic promise. “Mmm...did you think about this, Gwen?” Conan made his first direct pass over her and Gwendolyn twitched. “Did you dream about us fucking? Because I did…” Beard chafing as he kissed around to the other side of her face, Conan emitted a low sigh. “I fantasized about you constantly.”

“Yes, sir.” Gwendolyn swerved her pelvis, slickening beneath Conan’s touch. “Fuck...I...so many times…”

“Mmm...tell me…” Conan whispered, fiddling faster as he dragged his pristine teeth over her skin. “Tell me what you imagined.”

“I...I…” Breath shallow and spine curving, Gwendolyn blinked rapidly, wrists straining against the bond of Conan’s hand as he summoned the heat from her depths. “I thought about...about sucking your cock. Sir. All the time.  _ Yes! Fuck!”  _

Thighs squeezing together, Gwendolyn clenched her eyes as the zaps overtook her curvaceous body. “Oh yeah?” Conan raced over her swollen clit, lifting to capture Gwendolyn’s lips with a satisfied snicker. “Mmm...you love sucking cock, don’t you?” Gwendolyn started seizing beneath him and still, Conan persisted, kissing her panting mouth. “If I make you cum, will you let me put my cock in your throat? Huh, Gwen? Huh?” 

“ _ Yes, sir! Yes! Fuck! Fuck!”  _ Shudder erupting over her, Gwendolyn’s heels kicked the arm of the couch, Conan smile brimming with accomplishment. 

“Mmm...yeah.” Retracting, Conan sat up, sucking the glowing fingers into his mouth salaciously before he rose to shed his pants and boxers. Gwendolyn stared in awe for a moment at his erection, thick and heavy hanging beneath his navel before Conan flopped down again, fingers threading through her red locks with a grin. “You want to suck me, Gwen?”

Green eyes drunk with lust, Gwendolyn knelt beside him and enclosed her fingers around Conan’s massive cock. “Yes, sir.” Lips encasing him, Gwendolyn worked her way down Conan’s shaft with a hum, Conan’s long fingers weaving into her hair as she cupped a hand over his balls and hollowed her cheeks. Bobbing into a rhythm, Gwendolyn let the saliva pool around Conan’s root as she sheathed him in the moist heat of her throat, tongue whipping around the wide head every few rises and relishing the high vulnerable notes that crept into Conan’s moans.

“Oh  _ fuck...Gwen! Yes! Your mouth!”  _ Conan writhed on the cushion beneath her, dexterous fingers gliding over her back to inch between Gwendolyn’s thighs, painting through her dewy pussy as she inhaled him. 

“ _ Gwen! Fuck!”  _ Containing himself enough to keep his hips flat, Conan’s nose flared and the muscle in his jawline popped as he gritted his teeth. “ _ Stop _ ...stop.”

Gwendolyn popped up, expression confused as she looked up at Conan’s face, fuschia with rapture. “You...don’t want to finish?”

“No, I just…” Conan glanced down her voluptuous body. “I want to do you at the same time. Come on…” Nodding eagerly, Gwendolyn stood and Conan laid down, patting his whiskered cheek with a grin. “Climb on.” Wedging one knee on either side of him, Gwendolyn took his cock in hand, preparing to resume her activities, but before she got her lips down, Conan’s lanky arms coiled around her hips, tugging her to his face with a groan.

“Oh...oh  _ fuck!”  _ Peeking between her legs, Conan’s lengthy tongue lapped with breakneck speed and Gwendolyn tightened in response, though she couldn’t escape the extreme sensation, his grasp unrelenting as Conan voraciously consumed. 

Gwendolyn jerked his cock, taking him halfway into her mouth with as much focus as she could muster, but it became virtually impossible to think about anything other than the decadent wonders unfolding between her legs as Conan’s beard rawed her thighs and she dripped over his eager face. 

Cock dropping from her shrieking lips, Gwendolyn lost control, hips slamming into his sturdy jaw. “ _ Conan! Fuck! Yes! Just like that! Fuck! Don’t stop!”  _ Gwendolyn clung to his thin thigh, unholy screams emanating form her as she helplessly quaked, radiant pleasure pulsing over her body. “ _ Conan! Conan! Fuck!” _

Spanking her with amusement, Conan’s appetite proved insatiable as he encased Gwendolyn’s engorged clit with his delicate lips, sucking until the sounds of her euphoria morphed into convulsing silence above him whilst he cracked a wide palm over her ass again, and again, and again.

Reduced to a quivering pile who could intone but one word ( _ yes...yes...yes… _ ) Gwendolyn’s eyeballs eventually found their way back inside of her skull and she gulped air, studiously grabbing Conan’s cock and craning back to him, voice hoarse.

“I want you to fuck my face.” The flurry between her thighs stopped for a second. “Sir.”

Muffled chuckle reverberating below, Conan nodded and Gwendolyn attacked his proudly perched cock with renewed vigor. Ensconcing him in the constrictive warmth, Conan groaned, hips tilting forward, the reversed angle providing him the addictive opportunity to explore unplumbed depths of Gwendolyn’s slippery throat.

Conan formed a hand over her skull, pelvis barreling forward as the continued sounds of Gwendolyn’s desire spurred him on. Sweet slurp around his paper-thin skin enthralling, Conan tossed his head back and forth, fingers replacing his tongue over Gwendolyn as he pounded his substantial cock into her willing face.

“ _ Oh fuck! Gwen! Yes! So good! Don’t stop!” _ Dancer’s legs pushing himself frantically up and down on the couch, Conan whined like an air raid siren, balls tightening and body flexing as he removed his fingers from Gwendolyn’s hair. “ _ Fuck! Fuck, Gwen! I’m gonna cum! Yes! Fuck!” _ Salty cum throbbing into her throat, Gwendolyn stayed down, swallowing every last drop and drinking in the intoxicating sound of Conan’s voice, high and needy, repeating her name.

Gwendolyn dismounted, the two of them collapsing exhausted on the couch before Conan tossed a weary arm over her shoulder. “Whew…” Conan wiped a hand across his beard before planting a kiss to Gwendolyn’s sweaty forehead. “That was great.”

“Yeah.” Smiling, Gwendolyn lifted her chin to claim Conan’s thin lips. “Maybe I should’ve encouraged you to do a shamelessly sexual promo a long time ago.”

**Author's Note:**

> Thank you for taking the time to read! If you enjoyed this story, please leave a comment or come say hi on tumblr at fandomtransmandom. I also accept requests!


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